The deal was supposed to pave the way for Apple to provide iPads for every student in the nation’s second-largest school system within the next two years, through a project estimated at $1 billion in all—$500 million for the devices and $500 million for infrastructure upgrades.

But the initiative was beset by problems from the outset … and soon the district was making headlines for all the wrong reasons.

It took just a week for nearly 300 students at L.A.’s Roosevelt High School to hack through security so they could surf the web unfettered on their new school-issued iPads. Similar problems emerged at two other high schools as well, and LAUSD officials immediately halted home use of the Apple tablets until further notice.

The incident prompted questions about how well district officials prepared for the tablet initiative—questions that were amplified by the dearth of training that teachers received.

What’s more, concerns were raised when it was revealed the iPads did not include keyboards. Shortly after the school year began, LAUSD announced that it might be spending an additional $38 million on wireless keyboard accessories.

Months before the problems arose in L.A., ed-tech consultant Alan November wrote about the importance of proper planning. He suggested that district leaders start not with the device, but with the learning in mind.

“If we don’t redesign the culture of teaching and learning and ask some fundamental questions about the design of learning environments, our investment in technology will be wasted,” November wrote. “Shouldn’t we define the problem as a learning design problem, rather than a technology problem?”